“So we beat on, boats against the current, borne back ceaselessly into the past.”
If you’re drawn to the opulence, mystery and bittersweet romance of The Great Gatsby, you’re certainly not alone. F. Scott Fitzgerald’s iconic novel captures the allure of wealth, the pursuit of the American Dream and the heartbreaking realities that often accompany it. The story of Jay Gatsby and Daisy Buchanan unfolds with decadence and tragedy, exploring themes that continue to resonate with audiences even to this day. But, what happens when you reach the end of Fitzgerald’s tale and find yourself craving more tales of love, ambition and social status? Fret not, we here at What We Reading have you covered with our list of books like The Great Gatsby! From classic American literature to contemporary novels brimming with Gatsby-esque flair, these stories capture the glamour and shadows of high society, offering readers the chance to experience the beauty – and heartbreak – of life’s grandest ambitions.
Tender Is The Night – F. Scott Fitzgerald
First up on our list of books like The Great Gatsby is Fitzgerald’s own follow-up to his acclaimed novel, Tender is the Night. The story follows Dick Diver, a charming psychiatrist and his beautiful wealthy wife, Nicole, as they attempt to navigate the emotionally-fraught world of 1920s European high society. Set against the stunning backdrop of the French Riviera, Dick’s seemingly idyllic life slowly unravels as his professional aspirations fade and Nicole’s own mental health deteriorates.
The pair’s marriage, already built on fragile foundations of wealth and codependence, becomes increasingly strained by betrayal, jealousy and self-destructive behaviours. As Dick continues to spiral into disillusionment and despair, Fitzgerald explores the costs of ambition, the lure of wealth and the illusions of happiness in the lives of the privileged.
On Beauty – Zadie Smith
Zadie Smith’s On Beauty is a witty and thought-provoking novel that explores family, identity and the clash of cultures through the story of the Belseys, a mixed-race family. Howard Belsey, a White British art history professor, is married to Kiki, a Black American woman deeply entrenched within the local community. Their marriage is defined by challenges, particularly Howard’s repeated infidelity which comes to light and causes deep strains.
The novel delves into the tensions between academic life, liberal and conservative values and the complexities of race and personal beliefs. On Beauty balances humour and insights in its look at family dynamics and social issues, demonstrating the beauty and messiness of human relationships, mirroring Gatsby’s own relationships and ambitions in The Great Gatsby.
Less Than Zero – Bret Easton Ellis
Clay returns home for Christmas vacation from his Eastern college and re-enters a landscape of limitless privilege where everyone drives Porches, dines at Spago and snorts mountains of cocaine. He attempts to rekindle his feelings for his girlfriend, Blair, and his best friend from high school, Julian, who has spiralled into a life of hustling and heroin. Clay’s holiday back home soon leads to a dizzying descent of desperation that takes him through relentless parties in glitzy mansions, seedy bars and underground rock clubs that unveil the seamy world of Los Angeles after dark.
Set in LA in the early 1980s, Bret Easton Ellis’ Less Than Zero is a raw and powerful portrait of a lost generation that experienced sex, drugs and disaffection at too early an age. It is undoubtedly one of the best books like The Great Gatsby for anyone looking for a read that captures the same themes of moral corruption.
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Revolutionary Road – Richard Yates
In the hopeful new age in the 1950s, Frank and April Wheeler appear to be a model American couple: bright, beautiful, talented with two young children and a starter home out in the suburbs. Yet, perhaps they started their new home and new family too early. Maybe Frank’s job is duller than he would like. And April never imagined herself in the housewife role.
Nevertheless, April and Frank have grown up believing that greatness is always just around the corner. Only that certainty has begun to be eroded. In one of the best books similar to The Great Gatsby, Richard Yates shows how Frank and April jettison their spiritual birthright, betraying not only each other but their best selves as well in his heartbreaking classic, Revolutionary Road.
The Vacationers – Emma Straub
For the Posts, a two-week trip to the pristine Balearic island of Mallorca with their extended family and friends is a celebration. Franny and Jim are toasting their thirty-fifth wedding anniversary; and their daughter, Sylvia has also just graduated from high school. The sun-soaked island, complete with its beaches and mountains, its tapas and tennis courts, also promises an escape from the tensions brewing back at home in Manhattan.
Yet, as Emma Straub unveils in The Vacationers, it does not take long for things to go awry. Over the course of the holiday, secrets come to light, old and new humiliations are experienced, childhood rivalries are unearthed and devastating old wounds are exacerbated.
The Secret History – Donna Tartt
Under the guidance of their mysterious and charismatic professor, a group of intelligent, wealthy and eccentric students study ancient Greek at a small liberal arts college in Vermont. The students form a close-knit but insular friendship. As they delve deeper into Greek philosophy and rituals, they become increasingly entangled in moral ambiguity and dangerous behaviours, which soon leads them down a dark and twisted path.
Narrated through the eyes of Richard Papen, an outsider to the group, Donna Tartt’s The Secret History is considered the defining dark academia novel and remains one of the best books like The Great Gatsby on the back of its haunting atmosphere, intrigue and themes of excess, identity and morality.
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The Marriage Plot – Jeffrey Eugenides
Jeffrey Eugenides’ The Marriage Plot is a coming-of-age novel set in the 1980s following three college friends as they navigate through love, intellectualism and the complex future looming ahead following their graduation. Madeleine is an English major caught between two men: Leonard, a brilliant but troubled biology student, and Mitchell, a religious and idealistic young man. As Madeleine’s relationships with both men evolve, the novel explores themes of love, mental illness and personal ambition, much like The Great Gatsby.
Eugenides explores the tensions between romance and intellectual pursuits, as well the many disillusionments that come with stepping into the world of adulthood. Delivered with wit and sharp insight, The Marriage Plot is a letter to the challenges of finding one’s place in a world defined so strongly by both personal desires and societal expectations.
The Interestings – Meg Wolitzer
The summer that Nixon resigned from the White House, six teenagers at a summer camp for the arts strike up an inseparable friendship. Decades on, their bond remains strong, but so much else has changed. In The Interestings, Meg Wolitzer follows these characters from the height of their youth through to middle age as their talents, fortunes and degrees of satisfaction diverge.
Epic in its scope and ambitious and populated by complex characters who are brought together and torn apart in a rapidly-evolving New York City, The Interestings is one of the most compelling books like The Great Gatsby for exploring the roles of class, art, money and power, and how all are able to swing over the span of a friendship and a life.
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Part-time reader, part-time rambler, and full-time Horror enthusiast, James has been writing for What We Reading since 2022. His earliest reading memories involved Historical Fiction, Fantasy and Horror tales, which he has continued to take with him to this day. James’ favourite books include The Last (Hanna Jameson), The Troop (Nick Cutter) and Chasing The Boogeyman (Richard Chizmar).
